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As the title says, I did do-release-upgrade today and have problem now. I've got this computer duel-booted with a win10 disk, and now the Kubuntu 19.10 install is unbootable. The disk has FDE, and even though I've mounted and decrypted my Ubuntu disk, boot-repair is not able to fix it, throwing the error Please use this software in a live-session (live-CD or live-USB). This will enable this feature.

This is the output for fdisk -l:

Disk /dev/loop0: 1.68 GiB, 1791954944 bytes, 3499912 sectors
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 512 bytes
I/O size (minimum/optimal): 512 bytes / 512 bytes


Disk /dev/sda: 931.53 GiB, 1000204886016 bytes, 1953525168 sectors
Disk model: ST1000DM003-1CH1
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 4096 bytes
I/O size (minimum/optimal): 4096 bytes / 4096 bytes
Disklabel type: gpt
Disk identifier: 90AA474C-403B-48D8-A51F-EA67103A29E9

Device       Start        End    Sectors   Size Type
/dev/sda1     2048    1023999    1021952   499M Windows recovery environment
/dev/sda2  1024000    1228799     204800   100M EFI System
/dev/sda3  1228800    1261567      32768    16M Microsoft reserved
/dev/sda4  1261568 1953523711 1952262144 930.9G Microsoft basic data


Disk /dev/sdb: 1.84 TiB, 2000398934016 bytes, 3907029168 sectors
Disk model: ST2000DM006-2DM1
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 4096 bytes
I/O size (minimum/optimal): 4096 bytes / 4096 bytes
Disklabel type: dos
Disk identifier: 0xab30ec36

Device     Boot   Start        End    Sectors  Size Id Type
/dev/sdb1  *       2048    1499135    1497088  731M 83 Linux
/dev/sdb2       1501182 3907028991 3905527810  1.8T  5 Extended
/dev/sdb5       1501184 3907028991 3905527808  1.8T 83 Linux

Partition 2 does not start on physical sector boundary.


Disk /dev/sdc: 28.96 GiB, 31071404032 bytes, 60686336 sectors
Disk model: USB 3.0 FD      
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 512 bytes
I/O size (minimum/optimal): 512 bytes / 512 bytes
Disklabel type: dos
Disk identifier: 0x48e7426f

Device     Boot Start      End  Sectors Size Id Type
/dev/sdc1  *     2048 60686335 60684288  29G  c W95 FAT32 (LBA)


Disk /dev/mapper/luks-d5504240-d15c-4453-8767-9beb20b9d785: 1.84 TiB, 1999628140544 bytes, 3905523712 sectors
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 4096 bytes
I/O size (minimum/optimal): 4096 bytes / 4096 bytes


Disk /dev/mapper/kubuntu--vg-root: 1.84 TiB, 1998602633216 bytes, 3903520768 sectors
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 4096 bytes
I/O size (minimum/optimal): 4096 bytes / 4096 bytes


Disk /dev/mapper/kubuntu--vg-swap_1: 976 MiB, 1023410176 bytes, 1998848 sectors
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 4096 bytes
I/O size (minimum/optimal): 4096 bytes / 4096 bytes

I attempted to run boot-repair once before decrypting it, and that broke it even further. Prior to the first attempt, I got the usual grub-rescue men, however now no OS is detected at all (despite all of my files being there, as I can confirm through the live-usb). I'm not really sure what to do now. I'd really rather not reinstall, if possible.

edit: Here is the boot report from boot-repair: https://paste.ubuntu.com/p/KSyx5WQtTv/

It seems that if I'm able to open this disk in my live session, it should be possible to fix the problem, since I'm able to see the /boot directory in sdb.

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Boot-repair is intended to be run from the LiveCD as it says. Make a LiveCD or Live-USB and use that. Or fix boot manually, as detailed in this related question. E.g. Boot through Grub rescue. (Type ls to get list of partitions. And then ls on each to find one with ext2).

set root=(hd0,msdos6)
set prefix=(hd0,msdos6)/boot/grub
insmod normal
normal

And then follow more detailed instructions in the above link for discovering and entering in the details for your particular setup, probably just

update-grub /dev/hdb
grub-install

(I put /dev/hdb instead of the usual /dev/hda, assuming your output of fdisk -l is showing the correct place to put /boot. Or wherever you want to put your Grub boot loader)

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I was able to solve the problem by following the solution given here: https://askubuntu.com/a/844231/591650

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